


Deadly Conversations

by dammndean



Category: Supernatural
Genre: Explicit Language, F/M, Jealousy, Reader-Insert, Smut
Language: English
Status: Completed
Published: 2018-12-03
Updated: 2018-12-03
Packaged: 2019-09-06 12:55:59
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 2
Words: 5,542
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/16833043
Author URL: https://archiveofourown.org/users/dammndean/pseuds/dammndean
Summary: Dean let's out some feelings he'd been holding in, feelings you tried to push down yourself long ago.





	1. Part 1

**Author's Note:**

> I was listening to Slaves and the song Deadly Conversations came on and gave me an idea for this story! I’ve linked the song and I’ll bold the parts I took from the song. Also, this is the first story I have ever posted here, so I’ll be random tagging. If you like the story and want it continued, let me know!

A light laugh leaves your lips at the joke this handsome stranger told you.

“So you’re funny and cute.. I can work with that,” you smile at him.

“Daniel.” He responded with a toothy grin of his own. 

“Y/N.” You replied, with that he winked back at you before turning to the bartender to ask for another round for the both of you. 

Your eyes left his dark ones and drifted over to your best friends green ones. He was sitting at the other end of the bar, as were you before you decided it was that time of the night where you all find your “partner” for the night. When you glanced at him you thought maybe he would be flirting with the cute blonde you had seen earlier, instead your eyes met Dean’s, he was staring right at you. The smile on your lips faltered a little bit at the intense gaze Dean was holding on you. His jaw was clenched tight and his knuckles were white from his hold on his nearly empty whiskey glass. 

“I’ll be right back, k?” You said softly to the man you were planning on spending the evening with. He made eye contact with you and smiled at you with a nod, letting you know he heard you all while leaning in for a small kiss, which you lightly returned. When you pulled back from the kiss he handed you your drink and you stood from your bar stool to head towards Dean. You noticed how he aggressively downed his drink and pulled his eyes from you to ask for another drink, all while clenching and unclenching his jaw.

“Where’s Sam?” You asked softly. Knowing your best friend well enough to know when something is clearly bothering him but he won’t talk about it.

“Dunno.” It was all he said before downing his recently filled whiskey and gesturing to the bartender for another. 

“Maybe you should slow down, it’s still pretty early out. How are you going to perform for some lucky lady later if you get whiskey dick, “ You joked, hoping to lighten his mood. He sat still, breathing in and out of his nose waiting for the bartender to finish pouring his 6th or maybe 7th whiskey of the night. When she walked away his serious gaze returned to you, making your smile disappear instantly. You sighed and sat on the stool next to him, not breaking eye contact.

"What’s up Dean?” You asked despite knowing the answer would be a gruff ‘Nothing’, “I can feel your eyes drilling into me from the other side of the bar.” His eyes cut to the dark eyed stranger waiting for your return. 

“Drilling into you huh? Like that douche bag over there will be doing to you later?” he said gritting his teeth. You were a bit taken back at that, this is what you all did. Finish a hunt, find a bar as close to your motel and take out pent up frustrations with a stranger before heading back to the bunker.

“I don’t understand what happened to put you in such a bad mood Dean but don’t take it out on me,” You said softly but sternly. "His name is Daniel. He seems nice enough, not a threat, will work for the night.” Explaining he shouldn’t worry about the man, he wasn’t a threat.

“ ** _Do you think I want to hear about your newest little thing? Well fuck that, and fuck the fact that it’s not me_**.” He downed his drink and slammed the glass back down. Standing to reach for his wallet. 

Your mouth hung open at his statement, “What did you just say?”

“I know you heard me, Y/N.” He said lowly. His eyes met yours again, then threw out cash on the bar, preparing to leave. “I’m heading back to the room.” He left the bar without a second thought and you sat there confused as you could be. 

When you finally got your brain to catch up with what just happened you sat down your drink and ran after him, Daniel forgotten. You saw him about half way to the motel you were staying at, seeing as it was just a few buildings down from the bar. You didn’t stop your run until you caught up to him. 

“Dean you can’t say something like that and then leave,” You said slightly out of breath. You grabbed his bicep to stop him. His back was still to you and you saw the tension in his shoulders. You slowly let go of his arm as you stepped in front of him. Your hands rested on his chest, trying to coax him to look at you. He stayed looking straight ahead but never tried to move away from you. 

"Go back to the bar Y/N.” Was all he said, voice void of all emotion. 

“I’m not going back to the bar, Dean. Not unless you come with me.” Hoping to just get him to sit and talk to you. 

“I’m not going back to watch you with him ** _. I don’t want to see you with someone else_**. I’m done.” He took at step back crossing his arms and pulling himself from you. 

He never was like this, he absolutely never showed any interest in you. It was him that almost made it a necessity to become okay with getting with strangers. The first few months of being with the Winchesters, adoring Dean and having to have your heart broken over and over again watching him, hearing him, seeing him with other women. You would spend all your off time together, whether it was making food together, drinking, listening to music, even binge watching Netflix and cuddling in his bed. It’s how you developed feelings for him in the beginning, but you quickly understood friendship is where it would end. 

You used to go with them for bar nights, because they would start so fun. You and the boys sharing stories over beer and shots and you’d get your hopes high that tonight would be the night he wouldn’t go find a girl but it never failed he would spot a cute blonde and be off. Most of the time Sam would stay with you, noticing your shift in mood. That was when you decided 'Enough is enough’, and started to allow yourself to open up and embrace when men came up to you. You started with heated make out sessions, then dabbling in some bedroom play. You hadn’t made the step to get past just heavy petting yet but you were doing what you were comfortable with.

“I remember the first time you did it.” He said through gritted teeth. Never uncrossing his arms or relaxing at all. 

“The first time I did what, Dean?” You mimicked his pose, crossing your arms, becoming more and more aggravated by the moment. 

“The first time you fucked a stranger.” Dean’s eyes wouldn’t meet yours.

Since when did he speak to you this way? He was always soft and sweet with you. It’s why your feelings for him grew so rapidly in the beginning.

“Are you being serious right now?” You were in disbelief. “You literally do _nothing_ but have sex with a woman you’ve known for like 5 minutes, how dare you even think you get an opinion on my sex life?" 

He rolled his eyes, "Whatever Y/N do what you want, go back to your little boy toy in there if it means that much to you.” He went to walk past you and you stepped in front of him. 

“You started this conversation Dean and I’m not ending it just because you are being rude to me. I know you and you’ve reached your max capacity of being honest so you think if you’re a dick to me I’ll let you go.” You reached up, plucking his chin down for some eye contact. Once his eyes meet your they soften just a little.

“Did you mean what you said?” Not hesitating to bring up his outburst in the bar. 

“Of course I did Y/N.. Every time I see you with someone else it tears me apart.” He said softly. 

“Where is this coming from Dean? I’ve been with you for a year.. Living at the bunker, being your best friend.. and you’ve never acted even a little interested in me. Why do you think I even started paying attention to other men, Dean?”

That sparked something in him, a surprised look on his face. 

“You expected me to sit and watch you have your way with whomever you please.. sit and wait for you to want me? Fuck that and fuck you, Dean.” Now you were the one that was done, you turned to head to the room, hell you may end up at the front desk just to ask for another room.

“Y/N, wait.. I didn’t mean..” He began before you cut him off. 

“Didn’t mean to want Dean? To assume I would sit around and wait on you forever? That I don’t have needs myself? To assume that I’ve fucked any of these guys?”, you nearly growled. 

“You mean you haven’t..” He didn’t finish his sentence. 

“Not that it’s any of your business, but no. I mean I’ve done stuff with them..” Dean had to draw in a deep breath at that, he didn’t like the idea of anyone even touching you. “You know me, Dean. I’m not super comfortable giving myself fully away to people.” You watched his face become less tense instantly.

“How much of a caveman are you, Dean? You don’t want anyone to have me, you never wanted me and all the while you get your fill of women. Why are you allowed to have a life but I’m not? The fact that I haven’t had sex since I met you shouldn’t make you happy.” You finished your statement with a small shove to his chest. Dean smiled down at you, you couldn’t believe he smiled! 

“Why in the hell are you smiling like an asshole right now?” You shoved him again. 

“You haven’t let anyone do _that_ with you?” He said with the smile still on his lips. 

“I’ve had sex before Dean! I’m a grown woman, I just haven’t found the right guy lately is all.” Why are you even defending yourself? How did the conversation even make it here.

“I think the right guy has been here all along Y/N, he was just being an idiot.” He stepped towards you, making you take a step back. He reached for and grabbed your wrists, coaxing your angry fists to relax, you slowly unclenched your hands and he softly intertwined his large hands into your much smaller ones. He tugged you closer to him You could only imagine the look on your face, to go from feeling so aggravated towards your best friend to this feeling of shock and joy. Your Y/E/C eyes met his emerald ones, even in the dark they pierced right through you. You couldn’t help but softly smile back at his big smile, making his eyes crinkle up.

“I haven’t been with anyone else in months Y/N. You’re all I can think about.” He confessed. Once of his hands left yours and you almost immediately missed the warmth. His hand came up to brush against your cheek and you leaned into it, eyes closing momentarily. 

“You’re so beautiful.” You’re eyes opened just in time to see Dean leaning in towards you, slowly enough to allow you to pull back if you didn’t want this. Your eyes flickered down to his full lips and back up to his.

“Dean..” your voice was soft and breathy. It wasn’t missed by Dean and he now knew you wanted this as much as he did. 

Your eyes didn’t shut until you felt his lips graze your lightly. You didn’t hesitate to kiss back,you felt his arms wrap around you pulling you closer to him, your hands were holding on tightly to his flannel, like if you let go you’d float away. You two stood there for a moment, enjoying being like this with one another, his hands made their way down to your ass and he didn’t miss the gasp you let out when he squeezed and tugged you even closer to him. It was like something in him snapped and this once sweet kiss quickly escalated to something more intense. His tongue begging for entrance into your mouth, you didn’t hesitate, letting him in promptly, your tongue and his fighting for dominance. Your hands went up to his hair, fingers delving into the short tresses and tugging lightly.

Dean pulled back with a moan, “Wanna go in the room baby?” He was out of breath, you weren’t sure if it was the lack of air from the intense kiss you shared or the kiss itself.

“Yes Dean, take me.. I’m yours. All yours”


	2. Chapter 2

**Notes for the Chapter:**

> This is the second (And I think last part) to this story! Hope you all enjoy.

“Dean..” His name was nothing more than a breath on your lips. He had you pinned between the freshly closed door to your shared hotel room, currently attacking your exposed next. Placing open mouth kisses and small bites over your sensitive flesh, enticing more and more breathy moans of his name to fall from your lips. You started pushing at his jacket hoping to quickly get him out of his clothes sooner than later. He pulled back from you, let his jacket fall to the ground and stood tall staring at you, his chest rising and falling rapidly. 

You smiled a big grin at him, regaining a bit of your composure now that he had detached himself from you. You slid your jacket and over shirt off and down your shoulders, landing on the floor behind you. Leaving yourself in your tank top and your hands went to your jeans to unbutton and push them off. It was then Dean smiled softly at you and stepped forward and placed his hands on top of your to stop their movement.

“Slow down sweetheart, we got all night.” He leaned towards you and softly placed his lips to yours in a soft and quick kiss to reassure you.

“I need you D.. now” You tried to lean back into the kiss but he softly chuckled and placed a kiss to your forehead.

“You got me baby, now and always.” You heart instantly fluttered at the honest words coming from your best friends, soon to be lovers, mouth. He noticed your moment of being taken back and he launched at the opportunity. He wrapped his arms around you and hauled you up over his shoulder, you couldn’t suppress the squeal that left your lips. His bowed legs took the few steps over to the bed before tossing you down onto it like you weighed nothing. You pulled yourself up to your elbows and Dean stood at the end of bed, placing his large hands on your upper calves, rubbing lightly for a moment before trailing his hands down, taking a moment to rid your feet of your shoes and socks. He sat quietly at the end of the bed to take his own boots off.

“You’re sure about this?” Why did you even say that? Why would you give him the option to change his mind? Because he is your best friend and if this whole thing got awkward or went the wrong direction you would be losing so much… too much. You noticed his back straighten as he kicked off the last boot and turned his upper half to you slowly. His soft green eyes met you and he carried a small frown, just barely tugging at the corner of his lips.

“Are you having second thoughts?” You didn’t miss the sad sound behind his voice.

“No!” Left your mouth a little too quick and loud. He smiled and you coughed to clear your throat, then repeat yourself, “No D, I want this… I want you. I just wanted to make sure this is what you wanted.”

He quickly pulled his socks off and tucked them into his boots and stood at the foot of the bed again. His hands went to your feet, lightly massaging them for a moment. Your eyes fluttered shut and a small moan of his name left your lips, his hands were magical.

“Do you have any idea how many times I’ve dreamed of you moaning my name?” Your eyes opened and met his green ones, he bit his lip and his hands moved up your legs over the top of your jeans. He placed one knee on the bed, then the next. One on each side of you as he slid his hands up the denim, only stopping when his hands met the soft skin under your shirt and right above your jeans.

“There is nothing in this world, in Heaven or Hell, that could make me change my mind.” His voice was thick with emotion, and you knew he was telling the truth. Your breath hitched at the confession but you quickly let out a big breathy moan when you felt his pink lips kiss the soft skin of your tummy right below your belly button.

“Fuck Dean, you can’t say shit like that and be that close to where I need you. You’re driving me crazy.” He gave you a signature Dean Winchester smirk.

“You better get ready baby because I’m just getting started.” Dean growled out.

His large hands firmly gripped your hips and his lips went right back to your lower stomach. Placing open mouth kisses, just letting you imagine what he could do to your most intimate area. Your hands went to his hair and gave a small tug, hoping to move this along, you were not as patient as Dean it would seem. He let out a low growl and pulled his lips from you and his hand moved to your unbutton jeans, he slowly unzipped them, sat up on his knees and started to tug the jeans off. You helped by kicking them from your feet. Dean smiled at your urgency, knowing you wanted him, needed him, as much as he wanted and needed you. He crawled up the bed and started kissing you again, trying to put as much emotion and feeling into the kiss that he could. You took it, not fighting to take over, just letting him do what he wanted to your mouth and when his kisses started trailing down your neck. Your hands went to his back, feeling the rough flannel under your fingers.

“D, you have entirely too many clothes on.“ Your words came out just above a whisper, worried you wouldn’t be able to get the words out.

”I’m not going to argue with you there baby.” He grinned, a beautiful and full smile.

He sat up for a moment, and it took all of 5 seconds for the flannel to be unbuttoned, slipped down his arms and into a pile on the floor. Then he did that super sexy, one handed pull from the back of his shirt to pull it over his head. He didn’t miss the hitch in your breathing and made a mental note of it. He tossed the shirt somewhere in the room, his eyes meeting your again. Once the shirt was off there he was, nothing but tanned, freckled skin. You’d seen Dean without a shirt, a perk of living together and sharing hotel rooms frequently. But now you get to look and feel freely and you had to seize the opportunity. He stood there for a moment, watching the way your eyes flitted all over his chest, taking him in. 

“Like what you see baby?” He said in true Dean Winchester fashion, cocky as ever.

Dean’s hand descended onto his denim covered erection and gave a gentle stroke over the material, hoping to find a small amount of relief. Also, the way you were looking at him wasn’t helping. He was straining against the material and he really wanted to release himself from the confines of his jeans, but he was trying to savor this moment.

“Let me see you.” You almost didn’t recognize your voice.

Dean’s eyebrows almost hit his hair line, surprised by your request. You were up on your elbows, lust blown eyes, locked onto where his hand was currently place. You didn’t care how desperate Dean saw you, you decided to be open and honest with him, and right now you wanted to see what _he_ looked like.

Dean growled out, with gritted teeth, hand grasping his hard cock through the material one last time. He gave you a curt nod, not thinking twice before he unbuttoned and unzipped the jeans. His eyes bore into your, you sat there almost out of breath, constantly reminding yourself to breathe. Dean already had such control of you and the night had just started. You sat patiently, legs clenching, trying to find any relief. The throbbing in between your legs only worsening when you saw the jeans fall down his thick legs, the thin cotton of his boxers not hiding his above average length from you.

Dean’s curious eyes were watching you just about writhe on the bed, clearly needing relief sooner than later. He could see your hard nipples through the fabric of your bra, and he definitely noticed the tightening of your legs, trying to alleviate some pressure between your legs. It was a sight to be seen, Dean had never been more turned on.

“Take off your bra baby.” Dean ordered out, and you complied.

He watched from the end of the bed as you leaned your self up into a sitting position before one of your small hands went behind your back to unclasp yourself from the confining piece of clothing. Your eyes flitted up to his as you let the straps fall down your arms, one arm holding the cups in place. You watched his throat bob up and down with anticipation, and it was your time to give him a smirk. Dean didn’t see it though, his eyes waiting patiently for you to reveal your bare breasts to him. You let the material fall to your lap before flinging it to the side.

Dean groaned at the sight of you, the swell of your breasts, the perkiness of your nipples. You looked better than he could have ever imagined. When your eyes didn’t quite meet Dean’s again, he noted the pink color that flushed your cheeks and could tell you were feeling vulnerable.

”Y/N, look at me.” Dean’s voice was stern, yet soft.

You brought your eyes to him, staring at his once green orbs that were almost black from the amount of pupil. You noted his labored breathing, eyes drifting down his body, past his thick chest onto his sexy stomach and stopped on his twitching cock. At some point he most of let the boxers fall down and you hadn’t noticed. You tried to will yourself to look away but you just couldn’t. There he was, for you to see, your previous apprehension was gone. He was thick and long, the tip slightly pink and you felt your legs involuntarily spread a little, you were so ready for him to be inside of you. Stretching you open in the best way possible. 

Dean bit his lip at your reaction, he noticed your body relax and legs spread, all for him.

“You think your ready for me baby?” Dean inquired. You nodded your head

“God, yes. Please D, fill me up.” Your voice was so breathy, so desperate but you didn’t care.

“Mm, I love the sound of that, but I think I need to open you up a little bit. Don’t you think? Make sure you’re all ready for me.” Dean grasped the base of his dick, willing himself to wait just a while longer, he had to taste you.

You couldn’t respond, you moaned at the thought and Dean grinned down at you before he started crawling back up the bed. Stopping when his mouth was right over your still clothed center, he placed one of each of his calloused hands on the inside of both your thighs, spreading them more and more until he was comfortably between them. He nosed at the apex of your thighs, and you moaned again. His lips planted the faintest kiss against your clit, you almost jolted from the gentle kiss. Your hips rose up, needing more from him. He chuckled at your neediness and leaned back to run his knuckled over your pussy, loving the low whines and moans coming from the contact.

”Dean I need more, please.” He was taking his time and you appreciated the build up but you felt at any moment you were going to burst. 

“I’ve got you baby.” He glanced at you once more before descending downward. 

Dean’s fingers pulled your panties to the side and licked a long strip all the way to the top of your clit and the noise it pulled from you knew you’d be getting complaints from the neighbors tonight.

“Holy shit, De-” You were cut off by his lips attaching themselves to your clit sucking hard before he started a rhythm of licked and sucking, nibbling and flicking. Making you a mess from his talented tongue.

Dean spent a good long while working you over, and he could tell you were getting close. His eyes flicked up to see you, never slowing his tongue, that’s when he started with one finger entering your hole, quickly. Taking you by surprise and it only took a couple of pumps from his finger before you were sent over the edge you had been teetering on. Your hands flew to his hair, tugging the short strands with name coming from your mouth a scream of pure pleasure. Dean didn’t stop, slowly adding another finger during your orgasm to work you through it, to heighten it for you and to also stretch you just a little more for his large member.

Dean groaned once you finally started to come down, your hands slowly releasing from the hold you had on his hair. His fingers stayed in your slowly pumping and he started kissing his way back up your body. You were reeling, trying to remember how to breath, the orgasm was mind blowing and you knew it would take a few moments before you could even think again.

“Wow…” Dean could hear the grin in your voice and he chuckled before his lips clamped softly around your nipple, drawing another moan from you.

You pulled on your legs up more, letting Dean settle himself between your thighs while he worked on your breasts, fingers slowly pumping in you still. You felt that all too familiar burn in the bottom of your belly again. Dean heard your breathing become labored again and he worked his way up your neck, stopping to suck at a spot that made you whine particularly needy. Dean added a third finger, curled them, hitting that stop deep within you and you knew you were about to cum again.

“D, please I need you.” Not wanting to cum again, without him deep inside of you.

“Cum now, Y/N” Dean had different plans. He hovered above you eyes boring into yours before you clamped your eyes shut the pleasure too intense.

“Fuuuuuck!” You screamed as you came for the second time in under 5 minutes, this orgasm so intense and so different from the last. You weren’t sure a man had ever given you two orgasms in one night much less this close together.

Dean watched you come down for the second time tonight and he was sure we would never get over the face or noises you made by his own hand. Your eyes finally opened to see his beautiful emerald ones flicking all over your face taking you in. You smiled at him and his eyes met yours once more.

“That was awesome.” You couldn’t help but laugh lightly, the euphoria still lingering all over you.

Dean chuckled too before reaching over the side of the bed, snatching up his jeans, finding his wallet and fished out a condom before settling himself back between your legs. He was back on his knees, leaning back to place the condom on, and you drank him in. You felt yourself getting more and more turned on, as if two orgasms isn’t enough, your body ached for him.

He make quick work of the condom, pulled your panties down and tossed them behind him. He laid back down over your, faces inches apart, his breath fanning over you face. He kissed you, thoroughly, his tongue leaving no part of your mouth untouched and it only made your body need him even more, you moaned in the kiss. Your arms braced on each of his strong arms, trying to root yourself in this moment. After what felt like a long time he broke from you for air. His hands moved to your hips, sliding them up past the swell of your breast, up your arms, before pinning your hands down to interlock your fingers. He softly kissed you again, pulling back just once more to ask again.

“You sure about this?” He had to know for sure that this is what you wanted.

You didn’t even let a moment pass before you responded with a resounding yes. Dean nodded before easing himself into you. You were so tight and he was certain fingering you open before was a good decision.

“Fuck baby, your tight.” Dean was showing restraint, so much so that he was gritting his teeth.

You could only moan in response as you felt him filling you up more and more, stretching you. It was glorious, the slight burn, the full filling and before too much longer he was deep inside of you. He sat there a moment, letting you adjust. You were ready though and you tried to move underneath him, hoping to spur him on.

“Move D, come on, need it. Need you.” You knew you didn’t make much sense but you couldn’t be bothered with worrying right now.

That was all it took to set Dean off and he started a fast pace a whole hell of a lot faster than he was wanting to take with you. He wanted to go slow and show you what you meant to him but there you were both chasing after your own release. Your walls were fluttering around his cock and you knew were close, so close. Only a moment passed before he knew what you needed and one of his hands left yours to rub softly on your clit and that was all it took. Two more thrusts he was choking our your name and you were loudly moaning his as you came together. His head was buried in the space between your neck and shoulder trying to bring himself down. And you were laying there a huge smile on your face, your heart hammering, breathe slowly becoming more even.

Dean lifted his head so that his eyes met yours and you weren’t sure which one of you had to biggest grin. He leaned down to kiss you, hands on each side of your face, putting the emotions of how he felt into the kiss.

Once he pulled himself from you he pulled himself from you and shuffled quickly to the bathroom, tossed the condom and came back with a wet rag to clean you with. You let out a small, shy, smile at him as he softly cleaned between your legs. After cleaning you Dean tossed the rag back into the bathroom before laying beside you on the bed, you both worked your way under the covers and just sat holding each other in a peaceful quiet. You almost felt sleep over take you.

That was until the door swung open and a clearly drunk Sam came stumbling in. He made his way over to his bed of the room before shaking his head, trying to regroup himself. That’s when he took in the state of the room, clothing everywhere, smell of sex in the air. His head whipped to the opposite before to see your eyes barely over the top of the covers where you were hiding your burning face. Then there was Dean who was kind of smug and kind of over protective. His arm wrapped around your naked frame pulling you closer to me.

“I am too drunk to do this right now.” It was all Sam said before collapsing on the bed, on top of the covers, completely clothed. 

You couldn’t help the giggle that bubbled up in your throat and Dean let out a laugh too. Your laughs died down after a while and you hear Sam’s soft snores. The laughing fit definitely didn’t bother him.

“I guess we have some explaining to do tomorrow, huh?” You smiled at him.

”So worth it thought baby, can’t believe you’re mine.” Dean wrapped himself around you more.

“Yours Dean, always yours.”


End file.
